How to Raise Money
Paul Graham's definitive essay on early-stage fundraising, distilled from watching hundreds of YC companies raise. Covers why fundraising feels harder than it is, breadth-first search weighted by expected value, getting to yes/no fast, and the dangers of raising too much or letting fundraising drag on.
On the Road to Recap: Why the Unicorn Financing Market Just Became Dangerous… For All Involved
Gurley's landmark analysis of the late-stage unicorn financing market: how dirty term sheets, valuation obsession, and the incentives of every player (founders, VCs, LPs, bankers) set up companies for painful recaps. Written at the top of the 2015-16 cycle and vindicated repeatedly since.
Reflecting on My Failure to Build a Billion-Dollar Company
Lavingia raised $8M from top VCs at 19, failed to hit venture-scale growth, laid off 75% of his team after a failed Series B, and rebuilt Gumroad as a profitable, deliberately smaller company. A brutally honest account of what happens when you take venture money and land on the 'good but not billion-dollar' outcome.
A Fundraising Survival Guide
Graham on the emotional reality of raising: why fundraising is demoralizing by design, why investors herd and stall, and how to keep morale and the company alive through the process. Written mid-financial-crisis.
Postmortem of a Venture-backed Startup
The CEO of Sonar (millions of downloads, ~$2M raised) explains the company's death: chasing engagement over growth, a failed nine-month attempt to sell rather than cut costs, and how investor incentives shaped the endgame. Read by over a million people.
My Startup Failed and This is What It Feels Like
Durkin founded 99dresses at 18, got into YC, lost her co-founders, and watched committed funding fall through at the worst moment, killing the company. An emotionally raw account of a collapsed round, visa pressure, and winding down.
Dear White Venture Capitalists: If you're reading this, it's (almost!) too late.
The viral 2015 essay, written while Hamilton was broke and pitching her fund, calling out venture's failure to fund underrepresented founders. It directly led to her first LP check and the founding of Backstage Capital.
Black Swan Seed Rounds
Altman observes that the best investments he's made were rounds nobody else wanted, and the hottest, most oversubscribed seed rounds mostly produced mediocre outcomes. Explains why consensus and quality are inversely correlated at seed.
What I Wish I Knew About Fundraising as a First-Time Founder
A former a16z partner turned founder describes how different fundraising looks from the founder's chair: what she got wrong despite knowing the investor side, and the gap between VC theory and founder practice.
The Anti-Portfolio: Honoring the companies we missed
Bessemer's famous public list of the legendary companies it passed on, with self-deprecating explanations ('friend rented her garage to Google's founders; David asked how he could leave the house without going near it').
How to Convince Investors
Graham on the substance of persuasion: convince yourself first, be a domain expert, and make the truth about your startup legible rather than performing confidence you don't have.
The Fatal Pinch
Defines the default-dead trap: moderate growth, months of runway, and an assumption investors will save you. Explains why bridge rounds usually don't come and what to do instead (cut costs or grow into default-alive).
Black Swan Farming
Graham explains power-law returns from the investor side: the best ideas look like bad ideas, YC's returns come from a handful of companies, and even professionals can't reliably pick winners at the time of investment.
How I Raised My $11.5M VC Fund
Yin documents raising Hustle Fund I with funnel numbers: hundreds of LP conversations, conversion rates, and tactics. Fundraising for a fund mirrors a startup raise, and she shows the whole pipeline including the rejections.
The Post YC Slump
Altman on the pattern where startups treat closing a round as the achievement, coast afterward, and die: fundraising success is a lagging indicator that buys time, nothing more.
Here's the Advice I Give All of Our First Time Founders
A First Round partner's standing advice to new portfolio founders, including how to work with investors after the round closes and how to set up the next raise from day one of this one.
Fundraising 101: I'm currently in NY! *Buys Flight to NY*
A young founder's candid, funny account of the performative side of fundraising: manufacturing 'I happen to be in town' moments, reading investor signals, and the theater everyone pretends isn't happening.
Reflecting on My Failure to Build a Billion-Dollar Company, Part 2
An analytical companion to Lavingia's essay: Baschez unpacks the structural reasons venture-backed Gumroad 'failed' at billion-dollar scale while succeeding as a business, examining how funding choices define what counts as success.
Is It Fair To Tell Founders 'Just Execute And You'll Be Fine' When We Know It's Not A Level Playing Field?
A sitting VC interrogates his own industry's meritocracy narrative: standard fundraising advice assumes network access and pattern-matching benefits that underrepresented founders don't get, and he discusses what honest advice looks like instead.
Out of the picture: why the world's best photo startup is going out of business (Everpix)
The definitive reported account of Everpix's death: a beloved product with paying users that ran out of runway mid-raise; the founders later open-sourced their pitch decks, metrics, and investor pipeline. A masterclass in how good products die from failed fundraises.
Mattermark Has Raised $2M in Our Second Seed Round
Morrill explains publicly why Mattermark took a $2M second seed instead of the Series A she'd been pitching: two years of nonstop fundraising, a bridge from a customer-investor, and the honest math of raising below your hopes.
Getting Out of the Startup Rat Race
After raising a $500K seed and then nearly running out of money, Pigford describes negotiating with his investors to reset expectations and step off the venture growth track, with the actual numbers Baremetrics published all along.
Dear SaaStr: What Are the Top Mistakes You See New Founders Make?
Lemkin's blunt list of first-founder mistakes, the fundraising ones foremost: assuming the next round is guaranteed, burning to a plan that requires it, and wasting months pitching the wrong investors.